


Remember Those Times I Was Hoping For Something?

by jeffannies



Category: Community (TV)
Genre: F/M, Fake/Pretend Relationship, Post Season 6, Reunited and It Feels So Good, School Reunion
Language: English
Status: Completed
Published: 2019-11-15
Updated: 2019-11-15
Packaged: 2021-01-31 12:21:29
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,066
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21446131
Author URL: https://archiveofourown.org/users/jeffannies/pseuds/jeffannies
Summary: She tries to not look surprised as she stares at him because now that the words are out there, the lie has been told, and it’s even worse to admit it’s not the truth. It’s even more embarrassing to be caught out in a little white lie – one he’s told to help defend her, no doubt - than having her old rival (and whoever else is here tonight) thinking that Annie is perpetually single.Jeff decides he'll be Annie's fake boyfriend for the night, and she's not going to turn that offer down.Set 4 years after Season 6.
Relationships: Annie Edison/Jeff Winger
Comments: 12
Kudos: 300





	Remember Those Times I Was Hoping For Something?

**Author's Note:**

> A big thank you to @littlemsnerd26, my wonderful beta reader, for helping me shape this story. It wouldn't be here without your guidance!

"Hi, Jeff… Um. It's me, Annie… Annie Edison?" she speaks into the phone, finding it hard to mask how nervous she is. She hopes he can’t hear the shakiness of her voice; hopes he’s not questioning why it’s taken her this long to reach out to him.

"It's been a while, hasn't it?" she laughs briefly. "I hope you're doing ok... When you get this message, call me back! It’ll be nice to hear from you."

Setting her phone on the counter, she sighs loudly. She’s spent the better part of a week debating whether or not to call him, whether it’s inappropriate to ask him for a favor, considering they haven’t seen each other in years.

The last time she saw him, he was dropping her off at the airport, a promise of something lingering between them, a promise that was then broken. After their goodbye kiss in the study room, one that she still thinks about to this day, she thought maybe things had changed between them. Yet once she was out of Colorado, it was like everything that happened between them in their last few days together, their final kiss and the bittersweet goodbyes, were all just forgotten about.

It’s her fault that nothing ever happened really. She’s the one that drifted away from Greendale, from their little makeshift family, from Jeff… But then again, she supposes he never tried to stay in contact with her either, so she’s not the only one to blame.

It doesn’t help that she has been out of state for the majority of the last four years. Between her FBI internship, electing to finish her degree in D.C., working her way up in different state bureaus until she _finally _stumbled her way into the Colorado Bureau of Investigation a few months ago, she hasn’t had the time to commit to a Greendale reunion. Her new job is a feat that she had posted to Facebook, hoping it might be enough of a hint to Jeff (and her other friends of course) that she was _home_, but he hadn’t said anything. Come to think of it, she didn’t think he had even liked the post. He must’ve seen it though, surely. Nearly _everyone _had congratulated her. Shirley sent her flowers, Troy and Abed called, hey – even Britta texted, and she was notoriously bad with online communication. What was his excuse?

Maybe it’s a sign he’s moved on, she thinks. Maybe he’s got a girlfriend now, or he even has his own little family. She knows his Facebook profile leaves a lot to be desired – he still thinks he’s too good for social media – and in the brief catch up calls they have had over the years; he never mentions much about his life. Come to think of it, she’s not even sure she knows Jeff anymore. Has he changed much? She’s not sure.

She starts to panic now. Maybe it is a big mistake reaching out now, especially to ask for a favor. It feels rude and, judging by the way she assumes he’s screening her calls; he doesn’t have the time for it – or her – anymore.

This whole Jeff situation is doing nothing to ease her anxiety. She’s been reeling in various states of anxiousness, overthinking everything since she received a Facebook notification inviting her to a Riverside High School reunion. The thought of being surrounded by people who called her “Little Annie Adderall” and made fun of her in her formative years is her idea of hell, but she thinks with a friend by her side, she could get through it. And that’s where Jeff comes into it all.

She asked Troy originally, but now that he’s out in California with Abed and in the middle of some big production project, he can’t attend. She tried inviting Britta, who remained elusive about her plans and refused to come. Shirley’s not an option, neither is Frankie. The only viable option is Jeff.

It’d be a good chance to catch up…

-

He calls her back 5 minutes later.

“Hey, Annie. What’s up?” he says ever so coolly. It takes her back to old times, where calls like this were common, or at least more frequent than they are now. Now she only calls him when she needs something, or when prompted by that Facebook Birthday notification and she feels so guilty about it.

But he sounds calm, unaffected by the stressful message she just left him, not bothered by the fact he hasn’t heard from her in, well, a _long _time.

There’s something about his voice… It instantly soothes her in ways she has long forgotten it could. A surge of emotion rolls over her and demands to be felt, feelings that she has been depriving herself of for some time.

She takes a deep breath, forcing herself to be strong. _You can do this, Annie._

"Hi, Jeff. I’m sorry to call you out of the blue like this…”

He doesn’t respond so Annie continues.

“Are you free next Friday? I need a favor.”

There’s a brief pause. His side of the line is silent for just a moment, and when he speaks again his voice sounds soft and hesitant. “What is it?”

“Would you come with me to my high school reunion?”

He scoffs over the phone. “I didn’t even go to _my _high school reunion, Annie.”

She huffs, trying to think of what to say. Back in their Greendale days, all she would need to do is pull out that one look he could never say no to. Annie could bat her eyelashes and pout ever so slightly and Jeff Winger would be putty in her hands.

But times have changed. And as he couldn’t even see her, she knows she has to pull some sort of Winger speech™ out of thin air and hope it works.

“_Please,”_ she starts with a pleading tone. “I _really _don’t want to go alone, and it would be so much to me having you by my side.”

He hums down the line.

She finds herself biting her nails in anticipation of his answer. He pauses for longer than she’d like him to, and she finds herself growing more anxious, wishing he’d just give her an answer. Unable to control herself, she starts talking again, hoping she sounds persuasive.

“It would be a great chance for us to catch up too. It’d be nice to see you again.”

“I mean I couldn’t think of anything worse to do on a Friday night,” he starts, and her stomach drops. Her eyes well up and she can feel her throat closing in.

“But fine, for you. When is it?”

She smiles wide, grinning into the phone as she holds it flush against her cheek.

“I can’t thank you enough.”

“You could try.”

-

When the day comes around, Annie can’t stop herself from pacing around her tiny apartment, her heart racing in her chest. She applies and reapplies her lipstick five times in the mirror, and fiddles with her hair, then her necklace, then her hair again as she waits for the optimal time to leave. She’s already checked the journey on the map on her phone, and she doesn’t want to be too early.

Her mind wanders to Jeff – for what seems like the millionth time that week – and she thinks about what he might be wearing, how he might look after all these years. She wants to know how things work between them now, whether or not they’ll fall into old habits and patterns and spend the night dancing around each other like they used to, or if conversations will be stilted and awkward and it’s a big mistake thinking otherwise.

Seeing Jeff tonight is not the only thing that’s causing her anxiety, however. She’s also worried about what might happen tonight with her old classmates. There’s a reason she doesn’t stay in contact with a lot of them, and yes, she may refrain from liking some of their achievement posts and life changes on Facebook for some bitter reason, but they deserve that _and more _after how horribly they treated her.

Is it really worth attending this thing, unsure what scars will be surfaced between her and her high school foes, or even her and Jeff? Has she just made a big mistake? Is it too late to back out?

She knows she wants the chance to prove herself at least. That’s important to her. She wasn’t voted “most likely to succeed” whilst at rehab for nothing – and now she’s got an incredible career, a pretty ok apartment, and a better fashion sense, she’s come a long way since she was the Annie they remember her as. It’s time to show all those jerks she went to school with that Annie Edison had grown up and made something of herself, which is probably more than most of her ex-tormenters could say. _Take that, idiots!_

Her thoughts are interrupted by a loud, resounding buzz. Her phone lights up: **REMINDER: Event starts in 30 minutes.**

Her stomach turns as she grabs her purse and smooths out one last invisible crease on her dress.

It’s a smart, black number she’s had picked out for a while, knowing it accentuates all the right assets while still looking demure and appropriate, perfect for the occasion. She smiles to herself, daydreaming about what Jeff will think of her little outfit. She tries to imagine his reaction, whether he’ll smile up at her in that soft grin she’s always loved, or if his smug smirk will appear and he’ll make some sort of smart comment about it.

She inhales and steps out the door, shutting it firmly behind her. _Let’s do this._

_-_

After all these years, she thought Jeff’s power over her might have subsided, but no. She still very much feels that schoolgirl shyness she felt in her early twenties when she finally sees him again. The moment they catch each other’s eye, she longs to be next to him, to have him smiling down at her and inching slightly closer whenever they’re alone and he thinks she won’t notice.

From the minute she spots him, she feels her stomach stir with the familiar buzz of butterflies, ones that no other man has ever been able to awaken within her. Her heart stops when their eyes finally meet in a long, tender gaze.

As they both take small, tentative steps towards each other in the parking lot, they find each other halfway, both grinning ear to ear. She hasn’t quite found the words to say to him yet, overwhelmed with the sight of her first _love, _Jeff Winger, standing right there, in the flesh. He’s hardly changed. Sure, his hair is splashed with a faint silver color, but he’s still as attractive as the day she met him. 

Her cheeks hurt from smiling so much already

“You look beautiful, Annie.”

She tries to hide her blush as his eyes linger on her body. His gaze burns against her skin, and she follows as his eyes trace around her waist, down her legs and back up again. She licks her lips slightly, feeling a wave of excitement roll over her. All those nerves have disappeared, drowned by a new thrill that only Jeff can stir up.

It’s ridiculous. She should be over this by now.

“Thank you,” she meets his eyes again now that the redness has subsided. “You look very handsome.”

And he does. He’s wearing one of those blue shirts that always look great on him. And even with the more defined crinkles around his eyes and the lines that have appeared since she last saw him, he’s the most handsome man she’s ever seen. He’s aged _very_ well. She has to stop herself from looking at him too much, just in case she can’t control the urge to kiss him. She _can’t_ embarrass herself tonight, and kissing Jeff probably isn’t her best idea, no matter how much she wants to do it.

“Let’s get this over with,” he says, extending his arm out for her to take. In response, she loops her arms through his.

The familiar gesture harkens her back to all the _milords _and_ miladys _and not-so-innocent hairbrained schemes, and, right now, she feels like she’s floating. She’s missed this. She’s missed him. 

-

“Annie Edison, and guest,” she says once they enter the venue, one she distinctly remembers for its red door. 

Memories flood back to that infuriating argument Jeff and Britta had years ago. He still insists on calling it L Street to this day. It’s funny how pointlessly argumentative the two of them could be, and it’s funnier how much Annie missed being witness to it all. They really did have to do something as a group sometime soon, it’s sad the way they’ve all seemed to drift apart as the years passed.

But just as much as Annie and her friends had shifted into a new world order, at the same time it seems like nothing in Greendale ever changed. The Red Door still sat proudly in the same place, as did many other local businesses, restaurants, as well as other haunts that Annie remembers from her younger years; she bets even Greendale Community College hasn’t changed much either.

They are waved inside, met with the buzz of various conversations held by faces Annie can vaguely recognize, and some she wishes she didn’t. She searches the crowd for friendly faces, frowning when she doesn’t spot one.

She holds on a little tighter to Jeff, anchoring herself into this weird reality she’s living. She feels like turning around and leaving now, wishing they had never set foot in there at all. _Maybe it’s a mistake coming here._ She doesn’t belong here.

“Jeff—” she turns to speak, to tell him to take her home, but she’s interrupted before the words can leave her lips.

“Annie? Annie Edison?” a woman approaches them, stopping Annie in her tracks.

She gulps.

It’s her old nemesis, Annie Kim.

Other-Annie’s stomach is swollen under her dress – she’s heavily pregnant, and her fingers glisten as her diamond ring catches the light.

“I arranged all of this,” Annie Kim gestures around the room. “You know, it was actually pretty hard considering I’m planning my wedding and we’re trying to build the nursery before the baby arrives. So much to do, you know.”

Annie Edison, the _original _Annie, nods.

“We moved back here after I quit my job in Washington, but then again, you know all about that, don’t you _Other Annie_.”

Annie (the _real_ Annie) wants to scream. As proud as she is in the way she’s excelled in her career, she can’t help but feel her achievements pale in comparison to _this. _A fancy house, a marriage, a baby on the way... She doesn’t even have _one _of those things, let alone all three.

And here was her sworn enemy, flaunting off her new perfect life. Why was the world so cruel?

“Hi Annie, you’ve done a great job,” she forces a smile, shaking the extended hand with as much fake enthusiasm she can muster.

“And look, you bought your _old _friend.”

“I’m actually her _boyfriend_ now,” Jeff grabs her by the waist, pulling her closer. “We’ve just moved in together, haven’t we?”

His eyes are on hers, shooting her a look she can’t ignore. While part of her struggles to hide her confusion, she has a compulsive need to laugh either out of awkwardness or shock.

She’s taken aback by the fact Jeff has called himself her boyfriend when she hasn’t seen him in years, and he has absolutely no reason to do so. And yet, he says it so willingly, acts like this fake relationship he’s concocted is something he’s not terrified by, a shocking fact considering the aversion he has always had to commitment.

Sure, it was a title she often wished he had, yet he showed no interest in being hers, so she gave that dream up a long time ago.

She tries to not look surprised as she stares at him because now that the words are out there, the lie has been told, and it’s even worse to admit it’s not the truth. It’s even more embarrassing to be caught out in a little white lie – one he’s told to help defend her, no doubt- than having her old rival (and whoever else is here tonight) thinking that Annie is perpetually single.

“I see. Good for you…” The other Annie says, sarcasm dripping out her mouth like venom.

“It is, isn’t it,” Jeff gushes beside her. She can feel her cheeks heating up as he watches the way he seamlessly pulls fictional memories out of thin air, fabricating stories and anecdotes that are sickeningly sweet and almost reminiscent of that old dream journal she had when she was 19.

She tells herself to remember that it’s just an act. The _real _Jeff Winger would never be this sweet and sappy. This is just his deceitful and convincing lawyer act he’s using, even if he is doing it out of sheer chivalry.

“Well _anyway, _I have to go greet other guests. Have fun you two,” Annie Kim offers a fake smile – but doesn’t bother concealing the eye roll she gives them as she storms off into the distance, and Jeff smiles smugly at her retreating figure.

“Thank god that got rid of her,” he sighs with relief. “Didn’t want to spend all night with the wrong Annie.”

She tries to thank him – or at least she means to – but Annie’s still a bit at a loss for words over this whole ‘fake relationship’ scenario. “So, you’re my boyfriend now?”

Her heartbeat speeds up as she utters the word. She hates that he has such control over her, even after all these years. Nothing and everything has changed between them, it’s confusing and exciting.

“Woah, are you breaking up with me?”

She rolls her eyes at him.

“You knew what she was doing. I was just trying to shut her up,” he shrugs noncommittally

For a moment, she thinks he’s going to leave it at that, until...

“Plus it’ll be fun. We can make up funny stories about each other to tell your fake friends… I’ll be a good friend and even let you do one at my expense.” he nudges her playfully.

“You don’t have to do this, you know.”

“I know.”

They stare at each other, almost daring the other to make the next move.

Jeff obliges, unable to ignore her famous Disney stare.

“C’mon Annie… Don’t act like you _haven’t fantasized _about it before.”

A rosy blush spreads across her cheeks as he teases her. “_Fine_. But if we’re going to do this, we need to get our stories straight.”

-

They saunter over to the bar together, arms still intertwined. Jeff orders their drinks, getting her a cocktail that takes her back to old times. He offers her the appletini and doesn’t even roll his eyes as she sips it happily, licking her lips when the straw falls out her mouth. He gets a beer, promising to stick to one drink and drive her home that night after he takes his first sip.

Then they discuss their game plan for the night – if anyone asks, they’ve been together for three years and they’ve just moved in together.

“So what about our careers?” she asks in the midst of the discussion, chewing on her straw absent-mindedly as she tries to work out the intricacies of their fake relationship.

“We can stick to our usual jobs, Annie. We’re not undercover.”

He’s laughing now, so she smacks him gently on the arm to stop him. He needs to be serious if they don’t want to get caught. Just one slip up could be the road to complete and utter embarrassment and Annie _really _doesn’t want that. Nothing can go wrong tonight.

“What I meant is that I don’t know what you do now,” she explains.

“I’m a consultant. I work for a few different law firms, depends on the caseload really,” he shrugs.

“That’s amazing, Jeff! Why didn’t you tell us?” she asks, she says, when what she means to say is why didn’t you tell _me_.

“I don’t know. I don’t share all this stuff on Facebook like you do.”

“So you saw my life update…”

“Of course I did, Annie. You share way too much online,” he snorts. “With all your Instagram, Facebook, Twitter… Snapchat posts, I can barely keep up.”

“Well, you watch it all, dummy.”

“I do.”

“The least you can do is comment on them or _something_. That’s what social media is for.”

He doesn’t respond. For a moment, she thinks she spots something like sadness in his eyes, but then it disappears.

“So why didn’t you ask to see me when you knew I was back in Colorado?”

He avoids her gaze for a moment. She watches intently as his brows furrow and he presses a hand to his chin in thought.

“I don’t know. I thought if you wanted to see me, you’d reach out. And you didn’t so…”

“It works both ways, Jeff.”

“I know,” he sighs.

“It’s ok. We’re here now. I guess that means something.”

“And there’s no one else I’d rather be the fake boyfriend of,” he wraps an arm around her shoulder, leaning his head against hers in a brief, blissful moment.

She has to remind herself that this is all an act and wonders how many times she’ll be having this conversation with herself tonight. She supposes there’s no real harm in it, it’s only a bit of fun… She just chooses to ignore the way her heart leaps slightly when she spots him staring at her in the corner of her eye, looking at her like he’s never seen her before, or like he needs to memorize her features. It’s intense, yet she doesn’t dare look away, otherwise, the moments gone and that fleeting feeling of happiness leaves with it.

“You know, this would be a lot more convincing if I had a ring on my finger or _something_,” she half-jokes as she sips on her second cocktail. Her inhibitions have slightly lowered, and this whole fake-dating thing is actually quite fun. If anything, Jeff’s just using it as an excuse to compliment her to strangers and Annie’s definitely not going to complain about that.

“Don’t worry about it too much, Annie. It’s all about the creative license. I know what I’m doing,” he says in true Jeff Winger fashion, like she had forgotten how convincing he could be. She still has some of his infamous Winger Speeches™ etched in her memory.

It’s dangerous how easy it is to fall into a pattern with him. It’s hard to ignore how good it feels when his arms are wrapped around her shoulders or holding on to her waist. His hand is warm and soft against her skin and she wishes there weren’t so many layers in between them.

Even when they’re not talking to someone, Jeff remains committed to the façade, standing extra-close, looking at her with playful, dark eyes. She hopes the night will never end.

The closer they get, the more they make each other giggle and laugh, the more she wants to lean up to him and kiss him. Her hands ache to feel the nape of his neck and the scruff of his hair against her skin, her lips want nothing more than to feel his, to taste him.

But before she can get anywhere near his mouth, she’s interrupted by three women calling her name. She frowns a little when Jeff pulls away slightly, letting the women pull Annie in for an embrace.

“Annie! Hi!” they coo at the same time.

“Jeff, this is Stacy, Lauren, and Lena. We were all in the Debate Club together. Guys… this is Jeff.”

She wouldn’t call them friends per se, but they’re probably the nicest people she will see tonight, so she’s not going to be rude to them. Still, she probably won’t lay it on too thick about the whole her-and-Jeff thing. She feels a bit bad lying to old peers.

“Ooooh, Jeff,” they all grin at him.

“Nice to meet you,” one steps towards him, twirling her hair around her finger.

“How do you know Annie?” another turns to him, a hopeful glint in her eye.

“I’m her boyfriend.”

“We met in college,” she helpfully adds, trying not to embellish on the story too much.

He continues, “It took me a few years to get the courage to ask her out, I’m not gonna lie. But now I have, I realize how lucky I am she ever said yes.”

He’s smiling down at her, and when their eyes meet, they both burst into the widest grins. They barely even register the people around them, even though the girls are aw-ing loudly at their words.

Annie really wishes this was all real because the butterflies in her stomach are going wild and he’s looking at her like he’s going to kiss her, and god, she hopes he does.

But he doesn’t. He just looks in her eyes like he’s trying to tell her something, and she wonders why he’s putting on such a good act. She even finds herself convinced of their story.

“I regret not doing it sooner,” he adds after a beat, and all the girls swoon in response.

“I’ve never seen you post about it on Facebook?” one inquires with a furrowed brow.

Jeff frowns, but Annie’s quick on her feet with a solution.

“Jeff’s not really a big social media person,” she explains. “I mean, his profile picture is a landscape for god’s sake! I try to get him into it but he’s just not a fan.”

The girls all burst into laughter, nodding as if that explanation makes sense. Jeff watches them in mild confusion. He still doesn’t get the big deal about social networking. He doesn’t have anything worthwhile to share.

“You guys are so cute,” the other smiles genuinely. “I’m so happy for you, Annie.”

-

The night continues similarly, women approach Annie trying to reintroduce themselves, and each time Annie and Jeff end up making ridiculous stories up about dates they had, their first kiss, what their apartment’s like. It comes too easily to them, almost as if were actually true, or as if they had prepared a script.

Maybe that is just in Annie’s head though. She can’t be sure.

Jeff has never been the romantic type. He’s certainly not the man to run in the rain to announce his feelings, or the type to write romantic poetry or a love letter to her – she gave up on those daydreams long ago. As for the Jeff she sees in front of her now, he’s a new man. Sure, he still won’t be writing sonnets comparing her to a summer’s day, and she won’t be humming tomorrow morning as she cooks them both pancakes like she always hoped to, but he’s describing the kind of dates she’s always dreamed of, and looking at her the way she always wished he would. If anything, she wants to know what’s changed.

It's a shame she won’t get to find out.

-

By the time they leave that evening, giggly and excited and still wrapped up in each other, Annie can barely believe the night is over.

“Did you have a good time?” he asks, wrapping an arm around her to keep her warm.

“I did,” she can’t stop herself from smiling. This whole night has exceeded her expectations and she wishes it wouldn’t end.

“You know what, I did too. Surprisingly.”

“I’m glad I’m not bad company,” she lets out a slight giggle,

“Mmm,” he nods in agreement, eyes lost in hers.

She finds herself unable to look away, a familiar pain in his eyes. Her heart pounds in her chest as she watches him, knowing that the moment she looks away this might all be over, and she’ll never feel quite like this again. That her special moment with Jeff Winger might be long gone, never to return. She can’t bear that thought.

“Jeff,” she starts but finds herself at a loss of what to say. How does she ask the man she’s been in love with since their moments of _something _during their college years if anything is ever going to happen between them? And now she’s back here, standing outside some bar in Greendale, wondering if he still feels the same.

Wondering if the time is _finally _right for them.

Hoping he’ll give her an open, honest answer this time, not like he did before.

“Yes, Annie?”

“Did you mean it? You know…”

He looks at her quizzically.

“What you said before… About us. Regretting not acting on it back then?”

He doesn’t answer, at least not with words. Instead, he slants his mouth on hers in one quick movement. He tastes like beer and smells like cologne (the scent she remembers from all those years ago) and when his tongue finds hers as he deepens the kiss, making her swoon into his arms.

It feels perfect, like fireworks erupting, or a perfect harmony. His stubble tickles her ever so slightly as their kisses grow more feverish.

“I meant it, Annie. Sorry that it took so long for me to realize,” he kisses her again, softer this time.

“You’re worth the wait,” she says breathlessly. She might have to pinch herself to be sure this is real.

“So… Do you want to be my fake girlfriend again sometime? You do owe me for tonight…”

“Jeff, that’s no way to ask me on a date…”

“_So demanding_,” he sighs, but he’s still smiling down at her goofily and she doesn’t even listen to what he’s going to say because her heart is beating in her ears and she’s overcome with emotion because _this is finally happening_. 19-year-old Annie Edison would faint if she knew Jeff Winger is currently stood in front of her, openly admitting how he feels for her.

“Annie Edison, do you want to go out with me? On a date? For real this time?”

Suddenly, she leaps onto him, her lips finding his in a passionate kiss, it’s safe to assume the answer is a wholehearted yes.


End file.
